The Guy
by RonsPigwidgeon
Summary: Castiel's boss is convinced that he would be perfect for her son, and is determined to get him to come to the Christmas party so they can meet. Castiel is still hung-up on his first and only one-night-stand. Or more specifically his dick.


**Author: **rons_pigwidgeon

**Rating: **NC17

**Pairing: **Dean Winchester/Castiel

**Warnings**: Masturbation, Dildos, Sexting, Anal Fingering, Anal Sex, Semi-Public Sex, Accidental Voyeurism, Unrequited Castiel/Meg Masters, Office Sex, Comeplay, Facials

**Summary: **Castiel's boss is convinced that he would be perfect for her son, and is determined to get him to come to the Christmas party so they can meet. Castiel is still hung-up on his first and only one-night-stand. Or more specifically his dick.

**Notes:** Story based off a tumblr prompt: My boss is always telling me how perfect her son would be for me and she promises he's coming to the next holiday party and don't worry he's heard all about me too and ALSO there's this dude I slept with once a couple of months ago and sometimes he still sends me dick pics when I ask him at 3 in the morning cause seriously dude's got a good dick AU

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><p>Looking at dick pics on his phone probably isn't the most productive use of his time, but it's either this or take a smoking break, and he promised his mother he'd quit by Christmas. He puts the phone on sleep when Mary walks by and tucks it in next to the framed picture of him and his brother in New York last year.<p>

"You haven't RSVP'd to the Christmas party, Castiel," she says, leaning over his cubicle wall.

"I had to check with my brother first. He's flying in for the holiday, but he wasn't sure what day."

"And?" She raises both eyebrows, leaning closer into the cubicle.

"He'll be coming in the 20th."

"Then, you'll be free?"

Part of Castiel wants to say no. He loves his boss dearly, but she's been talking up her mystical perfect son to him for almost a year, and Castiel knows the son will be at the party. If he and Castiel don't hit it off, it's going to be incredibly awkward. He has no other reason to say no, though, and there's always the little voice in the back of his head that reminds him it's been over four months since he got laid. His eyes flick to the phone before he returns Mary's smile. "Yes."

"Yes!" She throws both arms up in the air in victory. "You're going to love Dean, I just know it."

A little flutter passes through his stomach as he watches her walk away with a spring in her step. He hopes he will.

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><p>Friday night, Castiel has finished off the rest of the Jack and is sprawled out on his bed with his boxers pushed down his hips, his dick in his hand, scrolling through the pictures on his phone. God, that cock is beautiful. He remembers the way it had felt, thick and hot in his hand, pushing at his throat until he gagged. The way it's owner—the Guy, as Castiel has come to call him—had gripped his hips and fucked him so hard his head spun. He'd come so hard he had passed out for a minute.<p>

He licks his lips, sliding his hand up and down his lube-slicked shaft, letting his fingers creep down his perineum to rub against his hole, sliding one in, then two. He scrolls through the photos again, squirming on his fingers. The pressure's building, but it isn't quite enough…

**I need to see that dick again.** He sends the text without thinking, barely managing to use correct grammar, not that He cares.

A few minutes of humping his hand and he's rewarded with a reply.

The Guy:** you desperate baby?**  
>Castiel: <strong>wanna see it<strong>

He scrambles for the dildo he has hidden in his nightstand, fumbling with the lube before shoving it into himself. He chokes back a gasp as it rubs against his prostate. It isn't quite as long as The Dick, but it's close enough. A second later, there's a new text. A pic of the perfect dick, long and thick and rosy with blood. Castiel imagines licking a line up the smooth shaft, sucking on the head. Hands grabbing onto his hair and forcing him to submit as it slides further and further down his throat.

The next gasp is loud, quickly followed by a louder moan as he shoves the dildo harder and harder into his ass. He rolls over and gets up onto his knees, propping the phone up on a pillow so that he can look at it while he fucks himself. It doesn't take long, a few more thrusts and he's coming all over the towel he'd spread out underneath him, thick white cum spattering the green.

He falls over on his side, shaking with the aftershocks. The dildo slides out as he catches his breath. He takes a quick pic of the cum and the lube-slicked dildo and sends it to the Guy with a thanks. A few minutes later, he's cleaned up and asleep under the covers.

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><p>Castiel is hiding in the back corner, nursing a whiskey and hoping he might avoid meeting Mary and her son, when Meg finds him, Chesire grin of doom in place. "I hear the boss lady's looking for you. Don't wanna meet Dean-o?"<p>

Castiel scowls at her. "Would you?"

Meg cocks her head to the side. "No, but I'm not into grease monkeys." She sidles closer to him, invading his personal space to whisper in his ear. "I like 'em nerdy."

Castiel pulls away. "Not helping." He raises his glass to finish it off, only to discover he's already done so. "I'm getting another drink. Would you like anything?"

She holds up a champagne glass half-full. He nods and heads in the direction of the bar, eyes darting around the room for signs of Mary or her son. He's relieved to find none. Waiting for his drink, he feels someone walk up next to him and turns to find Him standing there. He's wearing a dark grey suit, tailored to fit perfectly, the collar of his shirt open to his throat. Castiel swallows, trying not to think about licking his collar bone. "Hi," he manages.

The Guy glances over at him, freezes for a moment, and then a sly, pleased smile takes over his features. "Hi there, fancy meeting you here." He moves closer, crowding Cas in a little against the bar.

"Yes… do you… work here?" It's a big company, and Castiel has a tendency to stay in the accounting department, away from the majority of employees. He feels heat rising up his chest, being so close to Him.

The Guy chuckles, shaking his head. "Oh no, I'm a mechanic. I'm just here for—"

"Dean, there you are! Oh, and you found Castiel for me. Excellent," Mary's voice interrupts, followed by Mary herself popping up next to them, beaming. "I see you've already introduced yourselves."

Castiel stills, staring from Mary to Him and back again. Is she saying that his one and only one-night-stand and possibly the best fuck of his life is _Dean_? Mary's mystical, magical son? "You're Dean?" he asks, voice cracking.

Dean looks hard at him. "Castiel?"

Cas nods, unable to form words. Dean laughs, starting with a chuckle, but it quickly escalates to him hunched over, hands braced on his knees, tears streaming down his face. His laughter makes Castiel's stomach flutter.

"Dean, you're being very rude," Mary starts, but Dean shakes his head, holding up a hand to stop her as he straightens and uses his other hand to wipe his eyes.

"No, no, it's not what you think. We've uh…" He eyes Cas up and down with an appreciative glance. "We've met before."

Mary frowns. "Oh. When? You never mentioned it. I showed you his picture."

"Yeah, he uh… he looked different. No glasses." Dean seems to be distracted by looking at Castiel, slowly gravitating closer. Castiel finds himself swaying closer as well.

"I don't like to wear them if I'm not driving."

"They look kinda cute on you."

"Well, I see you appear to be doing just fine without my help. I'll leave you to it, then." Mary leans up and kisses Dean's cheek, diverting his attention for a fraction of a second. "Be good." She turns to Castiel with a bright smile. "I'm so glad I talked you into coming."

Castiel smiles at her, unable to help himself. "I am, as well. Thank you, Mary."

Dean is in his personal space before Mary's even disappeared into the crowd, hand sliding around his waist. "I knew you were an accountant. God, that's hot." He noses into Castiel's hair, making him giggle at the ticklish sensation.

"Are you fetishizing my profession, Dean Winchester?" It feels good to say his name, to be able to refer to him as something other than the Guy. It feels more intimate somehow.

"I'm gonna do a whole lot more than that. Soon as my mom stops spying on us, we're finding your office, and I'm gonna fuck that tight little ass of yours right on your desk."

Castiel's toes curl in his shoes from just the thought of that, and he has to grip his hand into a fist and think of his uncle Zachariah naked to will an erection away. "I have a cubicle."

"Even better. More chance to get caught. You'll have to be extra quiet."

Castiel lets loose a tiny moan. When he feels a glass nudged against his elbow, he takes hold of it and downs it in two swallows, Dean's laughter warm against his neck.

Twenty minutes later his pants are around his ankles and he's leaning over his desk, legs spread wide while Dean crouches behind him and sucks at his hole. Cas scrambles for something to hold onto, pulls Dean's suit jacket to him, stuffs part of it in his mouth to muffle his groans. Dean's tongue is wicked over his skin, flicking back and forth over his sensitive rim, one hand jacking his cock in rhythm.

Castiel pulls the jacket away enough to beg, "Dean please, I can't…"

"Patience." Dean pulls his mouth away, using a thumb to spread his spit over Cas' hole. Cas looks over his shoulder as best he can, sees the intent way Dean is looking at his ass, and has to pull the jacket closer again to absorb his moan. Dean's thumb is rough with callouses, but his touch is gentle, slow. Torture. He's fucking torturing him.

Dean buries his face back in Cas' ass, licking and sucking until Castiel can barely stay upright. Just as he's about to beg again, a heavy door on the other side of the room creaks open and closed, accompanied by a voice.

"Castiel?" Meg. Fuck. He hears her heals muffled by the carpet as she walks closer. He and Dean are still hidden behind his cubicle, but there's nowhere for them to hide if she comes any closer.

"I hope you aren't working to hide from Queen Mary's offspring. You're supposed to be having fun," she complains, getting dangerously close to his cubicle.

He knows she isn't going to go away unless he says something. He shushes Dean's attempts to keep him down and raises his head over the top of the cubicle wall, no-doubt flushed and sweaty. His hair's probably a mess from Dean's hands. "Not working, don't worry. I just needed a minute."

She narrows her eyes at him, standing just two cubicles away now. "What's going on?"

There's a deep sigh from the area of Castiel's knees and he feels a body press up against his back as Dean appears behind him. "What's it look like, Masters?"

Meg gapes at them, mouth actually falling open. "Cas, you whore! Didn't think you had it in you. Wow."

Castiel would answer, but he feels the blunt head of Dean's condom-covered cock nudging his hole and all he can concentrate on is pressing back into it. He melts into the rough fabric of his cubicle wall as Dean sinks home, eyes rolling back in his head.

"Unless you wanna watch us, get the fuck out," Dean snaps, hand gripping Cas' hip as he slowly slides back out. Cas lets out a whine, gripping the wall as the head of Dean's cock brushes against his prostate. He should be ashamed to let Meg watch this, but it's too good for him to care. He can care later, tomorrow maybe. Or Monday. He bites his lip and closes his eyes again, hiding himself away from Meg's heavy-lidded stare.

"Shit, are you fucking him right now?" she asks.

Castiel doesn't know what Dean's silent response is, but it is enough to have Meg retreating quickly, slamming the heavy door behind her. Cas buries his face in his elbow, face heating with embarrassment as well as the lust. He feels Dean's nose nudge against his ear, his lips soft on Cas' neck. "Okay?"

Castiel twists around enough to reach Dean, kissing him hot and hard. "Fuck me," he rasps, pushing his hips back.

Dean grins, pecks his lips, snaps his hips so fast into Castiel that he's forced onto his toes. "Yeah?"

"Dean…" Cas whines, burying his face back in his elbow to stop himself from screaming. Sparks of electricity flare up his spine as Dean begins to fuck him in earnest, holding nothing back. He gets so deep that Castiel could swear he can taste him in his throat. He feels himself begin to tremble, unable to control his limbs as his senses are overwhelmed with sensations of Dean, Dean's perfect cock, his warm hands, his hot breath on Castiel's neck, the wet hickeys he sucks into Cas' skin.

"I got you, baby," Dean whispers in his ear. "You can come for me." Castiel doesn't need much more before he's tumbling over the edge, spilling all over his desk as Dean rocks him onto his toes. He bites onto Dean's wrist where the hand is braced on the wall to keep his scream quiet. Dean grinds up into him, slow and relentless, teasing his over-sensitive hole as he recovers. His thrusts gain speed as Cas' tremors fade, each one driving deeper into him. "Fuck, baby, I'm gonna…"

Cas tries to pull away, pushing Dean's hips away, desperate to get on his knees. "Wanna taste it," he manages as he forces Dean out of him, drops to the carpet, and rolls the condom off in one quick sweep of his hand. Dean's cock is as smooth and perfect as he remembers, and he doesn't waste a second in wrapping his lips around it.

"Babe, no, it's not safe…" Dean protests, pushing at Cas' shoulder, but he doesn't put much force behind it. His face is scrunched, tense with the need to come.

Castiel pulls away just long enough to say, "Shut up, and give me your cum." It's enough to push Dean over, the first hot spray covering his chin. He catches the second in his mouth, grinning around the head as he swallows the load down, licking the remnants off the shaft. Dean watches him with heavy, lust-filled eyes, combing a hand through his thick hair, dragging him back to his feet when he's done. He swipes at the string of cum along Cas' chin and feeds it to him, watching as Castiel sucks on his finger. He leans in and kisses him, pulling the finger away and replacing it with his tongue.

"Fuck, you're hot," Dean mutters, dragging his lips down Castiel's chin, his hand drifting down to probe at Cas' puffy, used hole. Castiel holds onto his neck for balance and rocks back against his fingers. "Careful, I might fuck you again before we get outta here."

"Are we getting out of here?" Castiel asks, unable to stop himself from smiling. Dean wants to do this again, maybe more than once.

"Yeah, you think I'm stupid enough to leave you twice? Fuck no."

Castiel tries not to let himself hope, but his stomach feels like a swarm of butterflies have taken up residence and his heart is beating so hard it hurts. "Really?"

Dean leans down and kisses him again, leaving him with the feeling of being conquered, claimed. "Let's get out of here before Masters comes back with a camera."

Castiel drops his head to Dean's chest with a pained groan. "Oh god, she saw you fucking me…"

"She only saw the look on your face. I bet it was a sight to behold."

"Not helping."

Dean chuckles at him and slaps his bare ass. "Get your pants on. The faster we get outta here, the faster I can get you naked in my bed." Castiel scrambles to comply, wanting to be naked in Dean's bed as much as Dean wants him there.

They make an appearance back at the party, just long enough for Dean to say good night to his mother while Castiel hides behind him and tries to look like he hasn't just been fucked to within an inch of his life. Mary looks delighted that they're leaving together.

Castiel feels at home when he slides into the passenger side of the Impala. Dean drives with a hand on his thigh, teasing closer to his groin with every mile they put between themselves and the party. By the time they reach Dean's house, Castiel is hard again and considering asking to be fucked right there, but Dean has him out of the car and in the house before he can say anything. The bed is soft, and Dean has him naked in it in under a minute. As Dean hovers over him, Castiel can't help but send a wish up that he will get to spend the rest of his nights with this man.

He gets his wish.


End file.
